Once upon a time, in a gritty, rent-stabilized land called the East Village of the late ’90s and early aughts, I introduced all my smart, interesting, kind, funny, straight guy friends to all my smart, interesting, kind, funny, straight girl friends, and they all got married and lived happily ever after.

This is the story of how I came to be known, far and wide, as the “East Village Yenta.”

Introducing people IRL — old school — was considered to be something of a major mitzvah even in those days. One of the harsher ironies of living in New York City has always been that even with the crushing multitudes of people, it can be incredibly lonely. It can seem impossible to find a mate. If you think meeting someone in New York City is hard now, I promise you, it was infinitely harder in the days before Facebook and Instagram and other social media made it standard to know pretty much everything about a person before ever meeting them.

So many single people, but so little context for knowing who was single, or for simply introducing yourself and striking up a conversation. How would you know whether the cute guy on the other side of the horseshoe bar at Vazac’s, who sort of smiled at you, or the one playing pool at Sophie’s, had a girlfriend? Or a boyfriend? Or if his relationship status might fall into the category of “It’s complicated?” In those days, it was particularly helpful to have an informed human vector pointing you in the direction of that special someone.

For a handful of couples in my East Village days, I was that vector. I tried to be subtle about it, creating low-stakes alternatives to that invariably awkward, inhumane fix-up standby, the blind date. I’d throw big parties, cramming forty or more guests into my un-renovated run-down East 13th Street tenement, for the express purpose of introducing just two of them in a low-key, dignified manner. I’d sneak a surprise guest into the exclusive weekly poker game I was part of, or into casual dinners with the group I came to think of as my East Village family, at 7A, or at one of the cheap sushi places in the neighborhood.

Sometimes I acted on my instincts almost unconsciously, making a last-minute phone call to invite someone along to a bar where I was meeting others, and it would invariably lead to a love connection. But in all situations, whether I was acting deliberately or inadvertently, there was one constant: I was always the one person in the room who knew both parties.

* * *

Mine was a full-service matchmaking enterprise. Not only would I introduce my friends, but in some cases, early in their courtships, before both parties were ready to consider themselves part of an “item,” I’d even chaperone them. Sure, I’ll be a third wheel on your road trip to a sleep-inducing community theater production of The Cherry Orchard in Bristol, Pennsylvania so that you don’t have to call it a “date.” Also included in the package was relationship advice for the unattached and lovelorn, which I’d provide for free. Ironic, considering that I myself was pretty consistently unattached and lovelorn, living, as I did, on a perpetual emotional roller coaster ride, courtesy of a coterie of ambivalent man-children, most of whom were complete jerks.

Occasionally my friends would try to return the favor. But while I loved introducing couples, I, myself, hated being fixed up. First of all, none of my friends were insecure or co-dependent enough to go to the ridiculous trouble I had for them, so awkward blind dates seemed to be the only option.

Second of all, in most cases, they wanted to introduce me exclusively to short dudes they had no one else to set up with. I’m a hair under five feet myself, so I’m not in any position to rule anyone out based on their height. But that’s not what this was about. I never had a problem with short guys. I dated men who were 5’2” and 5’3”. I also dated guys who were over six feet. The problem wasn’t the men’s lack of stature. The problem was, more often than not, it was the only thing we had in common. Having already logged more than my share of meals with short men who had no sense of humor, or had never read a book, I just wasn’t interested.

Third of all, in the cases where my friends did have great guys of any height that they wanted me to meet, I was forced to confront my aversion to…great guys of any height. No, not for me, the smart, interesting, kind, funny type! Let the other girls have them! I was in the market for a different breed of suitor: the rakishly cute, brooding, unreliable, sometimes mean, always broke, and decidedly broken species known as The Beautiful Mess, native to regions like the ’90s East Village. The anti-suitor. As if it isn’t already difficult enough in New York City to find someone to settle down with; try limiting yourself to the ones who are just not that into settling down. Or you. Or both. Stubbornly, I clung to this ridiculous preference way past the age when most women outgrow it.

If I was stuck in that groove way longer than I should have been, I hold New York City somewhat accountable. It provided me with too many compelling distractions from my misery and loneliness. New York is often anthropomorphized as a bad boyfriend who’s both hard to keep and hard to leave. But for me New York was more like my gay boyfriend, who wasn’t going to give me certain things you’d want in a relationship, but who would comfort me and cheer me up with shiny diversions when I most needed it. So much to see! Art, music, street fashion, architecture, crazy tourists. I’d walk around the lower tip of Manhattan on a Sunday afternoon after a bad date Saturday night, intrigued at every turn — interesting buildings, shops, a veritable UN of cuisines, people, people, people. The blessed profusion of variety tranquilized me. Afterward, my mind could remain occupied and my spirits high, at least until the man-child du jour would do or say something just subtly rejecting enough to throw me off balance. Where another woman might recognize this as a good stop to get off that train, I’d instead expend tremendous energy trying to decipher the mixed messages, and contorting myself into someone I imagined they’d be more interested in.

* * *

The people around me got tired of my tedious suffering before I did. The last straw was my 34th birthday dinner friends put together for me in October, 1999 at Jules on St. Marks Place. Bill, the on-again-off-again boyfriend I was, for some reason, living with at the time, had said no when I asked if he wanted to join my birthday celebration. My friends wouldn’t stand for it, though. They took matters into their own hands, calling Bill and persuading him to surprise me at the restaurant for cake.

Dinner and dessert came and went. We sat and sat. I wondered why my friends all kept looking to the door but not getting up and heading toward it. My friend Donna grabbed her Nokia cell phone and stepped outside. No one spoke. When Donna came back in, she couldn’t hide her anger.

“Bill is blowing us off,” she said. “He said he was going to surprise you and come for dessert. I’m so sorry, Sari.”

I hung in with Bill for another seven or eight months. I avoided my friends. I didn’t want to be lectured. I was crumbling inside, and I didn’t want them to see. And I wasn’t ready to walk away.

It hadn’t occurred to me that my friends might have been avoiding me, too.

“Buttons,” my friend Kevin said to me when I called him one afternoon — he was using one of his many affectionate nicknames for me — “I don’t know if you’ve noticed that I haven’t been spending so much time with you these days. It’s just that I can’t watch anymore as you put yourself through the ringer with guys like Bill. I can’t watch you as you keep staying.”

After a moment, I said, “I’m working on it, Kevin.” It came out more defensive than I wanted, but I didn’t know how to fix that, and I couldn’t say more words without crying. As soon as we hung up, the tears came rushing.

What Kevin had said hurt so much, but it was what I needed to hear. It was one of the most important things anyone has ever said to me.

It got me to dump Bill for good, and to then find myself a good New York shrink. And while I was busy getting my shit together, I made my next match, almost inadvertently.

I got a call from a guy I knew who’d moved from New York to Montréal the year before. His girlfriend, a lovely young woman I’d met at their going-away party across town at the Ear Inn, was now moving back to New York City. Without him. They’d broken up. Her name was Emily, and she was this pixie-ish, booksish dancer who also liked to write. She said she had just begun her first novel.

Emily was looking for a room to rent, and it so happened my friend Dave was looking for a roommate. I called them both and invited them to meet me for dinner at Jeoaldo, the cheap sushi place on East Fourth. When I hung up, the gears in my brain started turning. I made a third phone call, this one to Kevin.

Kevin and Emily married two years later.

As a daughter of clergy who rejects religion, I probably have no business invoking a Jewish adage about matchmakers. But it’s said that if you introduce three couples who go on to marry, a place is reserved for you at the highest level of Heaven. (Of course Jewish Heaven has different levels that you have to strive toward!) Kevin and Emily were couple number three for me.

Was it just a coincidence that after I introduced them — and, granted, after $20,000 worth of shrink sessions — that I then found my mate? That job I had to contract out; Nerve Personals served as my yenta — with the help of my gay boyfriend, New York City.

After we’d communicated intermittently on Nerve Personals for about six months but never met, I spotted Brian on East 7th Street, between Avenues C and D one morning when I was out jogging. He was standing behind his car, making sure it was outside the no-parking zone in front of a church entrance. I recognized him from his dating profile photo, and had enough context, obviously, to know he was single and in the market for a girlfriend. So, I said hello.

On February 5th, 2018, we celebrated our 13th wedding anniversary.

I’ll be forever grateful to New York City and its Alternate Side Parking Rules, and to Nerve Personals. And to Kevin, for a gift even greater than the mitzvah of matchmaking.